EP0657104A1 - Essbare Wasser-in-Öl-Mikroemulsionen - Google Patents

Essbare Wasser-in-Öl-Mikroemulsionen Download PDF

Info

Publication number: EP0657104A1
Authority: EP; European Patent Office
Prior art keywords: oil; microemulsion; water; surfactants; oils
Prior art date: 1993-12-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP93203463A

Other languages

English (en)

French (fr)

Inventor

Martin E. Unilever Res. Vlaardiningen Lab. Leser

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Unilever NV

Original Assignee

Unilever NV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-12-09

Filing date

1993-12-09

Publication date

1995-06-14

1993-12-09 Application filed by Unilever NV filed Critical Unilever NV

1993-12-09 Priority to EP93203463A priority Critical patent/EP0657104A1/de

1995-06-14 Publication of EP0657104A1 publication Critical patent/EP0657104A1/de

Status Withdrawn legal-status Critical Current

Links

239000004530 micro-emulsion Substances 0.000 title claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
239000003921 oil Substances 0.000 claims description 18
239000004094 surface-active agent Substances 0.000 claims description 14
239000004615 ingredient Substances 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 6
150000003904 phospholipids Chemical class 0.000 claims description 4
150000003626 triacylglycerols Chemical class 0.000 claims description 3
150000001860 citric acid derivatives Chemical class 0.000 claims description 2
150000003892 tartrate salts Chemical class 0.000 claims description 2
235000019198 oils Nutrition 0.000 description 11
239000007788 liquid Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
238000000034 method Methods 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
SUHOQUVVVLNYQR-MRVPVSSYSA-N choline alfoscerate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-N 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
102000014961 Protein Precursors Human genes 0.000 description 1
108010078762 Protein Precursors Proteins 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
229930003270 Vitamin B Natural products 0.000 description 1
229930003268 Vitamin C Natural products 0.000 description 1
229930003448 Vitamin K Natural products 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
-1 glycerol phosphatidylethanolamine Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
235000014593 oils and fats Nutrition 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002316 solid fats Nutrition 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
235000019156 vitamin B Nutrition 0.000 description 1
239000011720 vitamin B Substances 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/011—Compositions other than spreads

Definitions

This invention relates to an edible water-in-oil microemulsion.
emulsions For incorporating water and polar ingredients into edible oils emulsions can be used, usually resulting in cloudy or opaque products, although stable, clear liquids can be obtained by making microemulsions using a well selected combination of oils, polar liquids and surfactants.
US-A-5,045,337 describes edible W/O microemulsions using polyglycerolesters as surfactants, whereby up to 5% water can be incorporated into the microemulsion, although in the examples only 1% water is used. Attempts to incorporate more water resulted in not completely stable microemulsions. It would be desirable to make more stable microemulsions, having the possibility of incorporating more water and/or other polar ingredients and to use other surfactants being generally acceptable in the food industry.
thermodynamically stable transparent edible water-in-oil microemulsion comprising one or more oils, oil-soluble surfactants and polar ingredients characterized by up to 33% water and a surfactant comprising 0.1-30% of a diacylglyceride selected from the group of phospholipids and diacylglycerideesters selected from the group of citrates, tartrates and lactilates and 0.1-30% of a monoacylglyceride.
these diacylglycerides have a strong polar hydrophillic group.
the acylgroups in the surfactants are roughly of the same character as the bulk of the acyl groups present in the triacylglycerides forming the oil of the microemulsion.
diacylglyceride surfactants being phoopholipids and preferred monoacylglycerides being those having acylgroups with 8-18 carbon atoms.
Monoacylglycerides having unsaturated acylchains are in particular preferred.
microemulsions can in practice contain up to about 33% of water. When trying to increase this amount the emulsion turns turbid.
the lower level of water cannot practically be defined: any amount of water over the amount which is soluble in the oil-surfactant mixture will result in a microemulsion on mixing.
the amount of oil phase can vary from 20 to 99.8%.
oil in this specification and claims includes triacylglycerides (predominantly) and diacylglycerides of application. Consequently some solid fats may be dissolved therein.
the origin may be both natural and synthetic. Natural oils and fats may be vegetable, animal or marine origin, although the first source is preferred.
Microemulsions can be favourably used for incorporating oil-insoluble but water soluble ingredients into oils without changing the optical character of said oils.
ingredients being salts, sugar, aminoacids, vitamin B, C and K, flavours, flavour precursors, proteins, flavour boosters (eg. 5'-nucleotides) trace minerals, organic acids, peptides, and water soluble anti-oxidants and usually water contents up to 5% of the emulsion will be sufficient for this purpose.
the general procedure was as follows: the water soluble ingredients were dissolved in the water for the microemulsion and the surfactants in the oil. Any undissolved material was separated by centrifuging or filtration. Thereafter the clear liquids are combined and thoroughly mixed using a mixer.
Refined sunflower oil (88,49) was mixed with 10 g of a surfactant consisting of 1 g glycerophosphatidylcholine (PC) and 9 g glyceromono-oleate (GMO). After obtaining a clear liquid 1.6 g water is added and mixing was continued until again a clear liquid was obtained. Instead of water an 1:1 aqueous solution of 1 M glycine and fructose could be used.
PC g glycerophosphatidylcholine
GMO 9 g glyceromono-oleate
example 1 The process of example 1 was repeated using 32,5 g medium chain triglyceride oil (chain lengths 8-10 carbon atoms), 15 g PC, 20 g glyceromonocaprylate and 32,5 g water.
example 1 The process of example 1 was repeated using 20 g groundnut oil, 20 g PC, 40 g GMO and 20 g water.

Landscapes

Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Edible Oils And Fats (AREA)

EP93203463A 1993-12-09 1993-12-09 Essbare Wasser-in-Öl-Mikroemulsionen Withdrawn EP0657104A1 (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
EP93203463A EP0657104A1 (de)	1993-12-09	1993-12-09	Essbare Wasser-in-Öl-Mikroemulsionen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP93203463A EP0657104A1 (de)	1993-12-09	1993-12-09	Essbare Wasser-in-Öl-Mikroemulsionen

Publications (1)

Publication Number	Publication Date
EP0657104A1 true EP0657104A1 (de)	1995-06-14

Family

ID=8214201

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP93203463A Withdrawn EP0657104A1 (de)	1993-12-09	1993-12-09	Essbare Wasser-in-Öl-Mikroemulsionen

Country Status (1)

Country	Link
EP (1)	EP0657104A1 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002058480A1 (en) *	2001-01-25	2002-08-01	Unilever N.V.	Microemulsions
WO2003030650A1 (en) *	2001-10-08	2003-04-17	Kbig Limited	Cooking oils
ES2255864A1 (es) *	2004-12-23	2006-07-01	Natraceutical, S.A.	Proceso de microemulsion de antioxidantes polares en aceites comestibles.
WO2017162960A1 (fr) *	2016-03-23	2017-09-28	Lesieur S.A.S.	Emulsion alimentaire allegee en matieres grasses
CN111601511A (zh) *	2018-01-15	2020-08-28	菲仕兰坎皮纳荷兰公司	针对发泡系统优化的奶油组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0378893A2 (de) *	1989-01-17	1990-07-25	Kao Corporation	Essbare Öl-/Fett-Zusammensetzungen
US5045337A (en) *	1990-04-19	1991-09-03	The Procter & Gamble Company	Food microemulsion
WO1993012664A1 (en) *	1991-12-20	1993-07-08	Karlshamns Oils & Fats Ab	Heat-resistant chocolate composition and process for the preparation thereof

1993
- 1993-12-09 EP EP93203463A patent/EP0657104A1/de not_active Withdrawn

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0378893A2 (de) *	1989-01-17	1990-07-25	Kao Corporation	Essbare Öl-/Fett-Zusammensetzungen
US5045337A (en) *	1990-04-19	1991-09-03	The Procter & Gamble Company	Food microemulsion
WO1993012664A1 (en) *	1991-12-20	1993-07-08	Karlshamns Oils & Fats Ab	Heat-resistant chocolate composition and process for the preparation thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
AINO-MAIJA VESALA ET AL.: "Increasing the stability of vegetable oil solutions with the aid of monoglycerides and a cosurfactant", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY., vol. 62, no. 9, 1985, CHAMPAIGN US, pages 1379 - 1385 *
L. ENGSTRÖM: "Aggregation and structural changes in the L2-phase in the system water/soybean oil/sunflower oil monoglycerides", JOURNAL OF DISPERSION SCIENCE AND TECHNOLOGY, vol. 11, no. 5, 1990, pages 479 - 489, XP000431232, DOI: doi:10.1080/01932699008943272 *
L. MOBERGER ET AL.: "A study of fat oxidation in a microemulsion system", JOURNAL OF DISPERSION SCIENCE AND TECHNOLOGY, vol. 8, no. 3, 1987, pages 207 - 215, XP009006210, DOI: doi:10.1080/01932698708943603 *
MAGDA EL-NOKALY AND DONALD CORNELL: "ACS SYMPOSIUM SERIES 448 : MICROEMULSIONS AND EMULSIONS IN FOODS", 1991, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002058480A1 (en) *	2001-01-25	2002-08-01	Unilever N.V.	Microemulsions
US6716473B2 (en)	2001-01-25	2004-04-06	Unilever Bestfoods North America, Division Of Conopco, Inc.	Microemulsions
WO2003030650A1 (en) *	2001-10-08	2003-04-17	Kbig Limited	Cooking oils
ES2255864A1 (es) *	2004-12-23	2006-07-01	Natraceutical, S.A.	Proceso de microemulsion de antioxidantes polares en aceites comestibles.
WO2006070026A1 (es) *	2004-12-23	2006-07-06	Natraceutical Industrial S.L.U.	Microemulsión de antioxidantes polares en aceites comestibles
ES2255864B1 (es) *	2004-12-23	2007-08-01	Natraceutical, S.A.	Proceso de microemulsion de antioxidantes polares en aceites comestibles.
WO2017162960A1 (fr) *	2016-03-23	2017-09-28	Lesieur S.A.S.	Emulsion alimentaire allegee en matieres grasses
FR3049170A1 (fr) *	2016-03-23	2017-09-29	Lesieur S A S	Emulsion alimentaire allegee en matieres grasses
CN111601511A (zh) *	2018-01-15	2020-08-28	菲仕兰坎皮纳荷兰公司	针对发泡系统优化的奶油组合物

Legal Events

Date	Code	Title	Description
1995-04-28	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1995-06-14	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE
1995-06-30	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN
1995-08-23	18W	Application withdrawn	Withdrawal date: 19950623

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US5160759A (en)	1992-11-03	Edible oil-in-water emulsion
US3793464A (en)	1974-02-19	Process for preparing aqueous emulsion of proteinaceous food products
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US3505074A (en)	1970-04-07	Phosphatides and their method for their preparation
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AU2013376388A1 (en)	2015-08-06	Process for the manufacture of edible water-in-oil emulsions
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JPS57118755A (en)	1982-07-23	Production of food products containing emulsified fat